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Updated: Apr 21, 2026

Preparation of Stable Bicyclic Aziridinium Ions and Their Ring-Opening for the Synthesis of Azaheterocycles
Published on: August 22, 2018
Novel synthesis of the ABC rings of solanoeclepin A
Ya-Ting Lin1, Feng-Yi Lin, Minoru Isobe
1Department of Chemistry, National Tsing Hua University , 101, Section 2, Kuang-Fu Road, Hsinchu 30013, Taiwan.
Abstract:
A stereocontrolled synthesis of the ABC rings of solanoeclepin A has been achieved. The seven-membered ring B was synthesized by an intramolecular Prins-ene reaction between an aldehyde and an enyne-dicobalthexacarbonyl complex. The acetylene in this synthesis plays multiple roles: to join the A and C rings, to allow stereoselective cyclization via dicobalthexacarbonyl complexation, and to facilitate Nicholas cation stabilization followed by deprotonation to form an endo-cyclic olefin (Nicholas-Prins cyclization).
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